CN110804060A - Organic compound based on nitrogen-containing heterocycle and preparation method and application thereof - Google Patents

Organic compound based on nitrogen-containing heterocycle and preparation method and application thereof Download PDF

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CN110804060A
CN110804060A CN201910993202.3A CN201910993202A CN110804060A CN 110804060 A CN110804060 A CN 110804060A CN 201910993202 A CN201910993202 A CN 201910993202A CN 110804060 A CN110804060 A CN 110804060A
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organic compound
nitrogen
containing heterocycle
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toluene
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樊红莉
李风海
郭明晰
郑蕾
郭倩倩
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Heze University
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom

Abstract

The invention provides an organic compound based on a nitrogen-containing heterocycle, a preparation method and application thereof, and relates to the field of OLED materials, wherein the structural formula of the organic compound is as follows:

Description

Organic compound based on nitrogen-containing heterocycle and preparation method and application thereof
Technical Field
The invention relates to the field of OLED materials, in particular to an organic compound based on a nitrogen-containing heterocycle, and a preparation method and application thereof.
Background
The organic electroluminescence refers to a phenomenon that an organic material emits light when excited by a current and an electric field under the action of the electric field. Organic electroluminescent diodes (OLEDs) are a new generation of display technology that take advantage of this phenomenon to achieve display. Since the first excellent organic electroluminescent devices were manufactured by Tang c.w. and vansylke s.a. of Kodak corporation in 1987, organic electroluminescent displays have attracted much interest for their advantages.
The OLED has many advantages of self-luminescence, wide viewing angle, fast response speed, flexible display, etc., which makes it the most favorable competitor of the next generation of flat panel display technology and receives great attention from people.
At present, the red and green light emitting materials in the OLED have been commercially used due to their excellent properties, and blue light emitting materials with excellent properties are lacking. For common anthracene fluorescent blue light materials, the luminous efficiency is low; the lifetime is lower for phosphorescent blue materials such as Firpic. Therefore, how to design a new blue-light material for an OLED with better performance is a problem to be solved by those skilled in the art.
Disclosure of Invention
The organic compound has high structural regularity, higher luminous efficiency and high thermal stability, has good application effect in OLED devices, and has good industrialization prospect.
In order to achieve the purpose, the invention is realized by the following technical scheme:
an organic compound based on a nitrogen-containing heterocycle, the structural formula of the organic compound being as follows:
Figure BDA0002238925600000021
wherein R is1、R2Each independently is hydrogen, deuterium, cyano, halogen atom, substituted or unsubstituted C1-C20 linear or branched alkyl, substituted or unsubstituted C6-C30 aromatic hydrocarbon, substituted or unsubstitutedOr unsubstituted C5-C30 heteroaromatic hydrocarbyl;
L1、L2each independently is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl;
X1、X2、X3、X4、X5、Y1、Y2、Y3、Y4、Y5each independently is C (R)3)、N；
The ring A and the ring B are the same in structure or mirror images of each other;
R3is any one of hydrogen, heavy hydrogen, cyano, halogen atoms, C1-C4 linear alkyl or branched alkyl, C6-C12 aromatic hydrocarbon;
m and n are each independently 1 or 2.
Further, R1、R2Each independently selected from cyano, phenyl, anthracenyl, naphthyl, phenanthryl, 9-dimethylfluorenyl, 9-spirobifluorenyl, oxyfluorenyl and thiofluorenyl.
Further, it is characterized in that L1、L2Each independently is a group of the formula:
Figure BDA0002238925600000031
further, R3Is any one of hydrogen, heavy hydrogen, fluorine atom, methyl and phenyl.
Further, the organic compound is any one of compounds represented by the following structural formulas:
Figure BDA0002238925600000041
further, the preparation method of the organic compound is as follows:
Figure BDA0002238925600000052
adding the raw material (I), the raw material (II) and sodium carbonate into a mixed solvent consisting of toluene and water, stirring and uniformly mixing, then sequentially adding tri (o-tolyl) phosphine and palladium (II) acetate, heating to reflux, stirring and reacting for 10-15h, cooling to room temperature after the reaction is finished, filtering, separating toluene, extracting a water phase with toluene, combining organic phases, washing with water, drying, concentrating under reduced pressure to obtain a crude product, and purifying the crude product by column chromatography to obtain the organic compound.
Further, the mass ratio of the raw material (I), the raw material (II), sodium carbonate, tri (o-tolyl) phosphine, and palladium acetate (II) is 1:2-2.1:4: 5-10% to 1%.
The organic compound based on the nitrogen-containing heterocyclic ring is applied to the preparation of OLED devices.
An OLED device comprises an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode, wherein the light-emitting layer contains at least one organic compound based on the nitrogen-containing heterocycle.
The invention has the following beneficial effects:
the organic compound has a structure in which benzene rings on two sides are provided with benzo five-membered nitrogen heterocycles, the structure is a blue light structure with excellent performance, the blue light structure has a high triplet state energy level and a wide energy gap, the glass transition temperature of the blue light structure is high, crystallization is difficult, A, B two conjugated rigid aromatic rings are further introduced into molecules, the obtained compound has high structural regularity, high luminous efficiency and high thermal stability, and the carrier transmission is balanced.
Detailed Description
Example 1:
the synthesis method of the organic compound (1) is as follows:
Figure BDA0002238925600000062
adding compound 1-a (5g, 613.97g/mol, 8.14mmol), compound 1-b (2.1eq, 2.1g, 123.05g/mol, 17.1mmol) and sodium carbonate (4eq, 3.45g, 105.99g/mol, 32.57mmol) into a mixed solvent composed of toluene (100g, 20 times of the mass of compound 1-a) and water (100g, 20 times of the mass of compound 1-a), stirring, mixing, adding tri (o-tolyl) phosphine (5% eq, 0.12g, 304.37g/mol, 0.41mmol) and palladium acetate (II) (1% eq, 0.02g, 224.51g/mol, 0.08mmol), heating to reflux, stirring, reacting for 10h, cooling to room temperature, filtering, separating toluene, extracting the aqueous phase with toluene, combining the organic phases, washing with water, drying, concentrating under reduced pressure to obtain a crude product, purifying the crude product by column chromatography to obtain organic compound (1.04) (4.04), yield 81.1%), MS (EI) 613.2(M + H)+。
Example 2:
Figure BDA0002238925600000071
the synthesis method of the organic compound (4) is as follows:
Figure BDA0002238925600000072
adding a compound 2-a (5g, 916.11g/mol, 5.46mmol), a compound 2-b (2.1eq, 1.41g, 123.05g/mol, 11.46mmol) and sodium carbonate (4eq, 2.31g, 105.99g/mol, 21.83mmol) into a mixed solvent consisting of toluene (100g, 20 times of the mass of the compound 2-a) and water (100g, 20 times of the mass of the compound 2-a), stirring and uniformly mixing, and then sequentially adding tri (o-tolyl) phosphine (5% eq, 0.08g, 304.37g/mol, 0.27mmol) andpalladium (II) acetate (1% eq, 0.01g, 224.51g/mol, 0.05mmol), heating to reflux and stirring for reaction for 15H, cooling to room temperature after the reaction, filtering, separating toluene, extracting the water phase with toluene, combining the organic phases, washing with water, drying, concentrating under reduced pressure to obtain a crude product, purifying the crude product by column chromatography to obtain organic compound (4) (3.87g, yield 77.5%), MS (EI):915.3(M + H)+。
Example 3:
Figure BDA0002238925600000081
the synthesis of organic compound (15) is as follows:
Figure BDA0002238925600000082
adding a compound 3-a (5g, 1200.27g/mol, 4.17mmol), a compound 3-b (2.1eq, 1.08g, 123.05g/mol, 8.75mmol) and sodium carbonate (4eq, 1.77g, 105.99g/mol, 16.66mmol) into a mixed solvent consisting of toluene (100g, 20 times of the mass of the compound 3-a) and water (100g, 20 times of the mass of the compound 3-a), stirring and mixing uniformly, then adding tri (o-tolyl) phosphine (5% eq, 0.06g, 304.37g/mol, 0.21mmol) and palladium (II) acetate (1% eq, 0.01g, 224.51g/mol, 0.04mmol) in sequence, heating to reflux, stirring for reaction for 15h, cooling to room temperature, filtering, separating out toluene, extracting an aqueous phase with toluene, combining organic phases, washing with water, drying, concentrating under reduced pressure to obtain a crude product, purifying the organic compound (15.71 g), yield 74.3%), MS (EI) 1199.5(M + H)+。
Example 4:
Figure BDA0002238925600000091
the synthesis of organic compound (29) is as follows:
Figure BDA0002238925600000092
adding compound 4-a (5g, 896.07g/mol, 5.58mmol), compound 4-b (2.1eq, 1.45g, 124.04g/mol, 11.72mmol) and sodium carbonate (4eq, 2.37g, 105.99g/mol, 22.32mmol) into a mixed solvent composed of toluene (100g, 20 times of the mass of compound 4-a) and water (100g, 20 times of the mass of compound 4-a), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.08g, 304.37g/mol, 0.28mmol) and palladium (II) acetate (1% eq, 0.01g, 224.51g/mol, 0.06mmol), heating to reflux, stirring, reacting for 15h, cooling to room temperature, filtering, separating toluene, extracting the aqueous phase with toluene, combining the organic phases, washing with water, drying, concentrating under reduced pressure to obtain a crude product, purifying the crude product by column chromatography to obtain organic compound (29.79 g), yield 75.8%), MS (EI) 897.3(M + H)+。
Example 5:
Figure BDA0002238925600000101
the synthesis of organic compound (34) is as follows:
Figure BDA0002238925600000102
adding compound 5-a (5g, 716.05g/mol, 6.98mmol), compound 5-b (2.1eq, 1.80g, 123.05g/mol, 14.66mmol) and sodium carbonate (4eq, 2.96g, 105.99g/mol, 27.93mmol) into toluene (100g, 20 times of the mass of compound 5-a) and water (100g, 20 times of the mass of compound 5-a), stirring, adding tri (o-tolyl) phosphine (5% eq, 0.11g, 304.37g/mol, 0.35mmol) and palladium (II) acetate (1% eq, 0.02g, 224.51g/mol, 0.07mmol), heating to reflux, stirring for 15h, cooling to room temperature, filtering, separating toluene, extracting the water phase with toluene, combining the organic phases, washing, drying, concentrating under reduced pressure to obtain a crude product, purifying the crude product by column chromatography to obtain organic compound (34) (4 g), yield 80.2%), MS (EI) 715.3(M + H)+。
Example 6:
Figure BDA0002238925600000111
the synthesis of organic compound (42) is as follows:
adding a compound 6-a (5g, 716.05g/mol, 6.98mmol), a compound 6-b (2.1eq, 1.80g, 123.06g/mol, 14.66mmol) and sodium carbonate (4eq, 2.96g, 105.99g/mol, 27.93mmol) into a mixed solvent consisting of toluene (100g, 20 times of the mass of the compound 6-a) and water (100g, 20 times of the mass of the compound 6-a), stirring and mixing uniformly, then adding tri (o-tolyl) phosphine (5% eq, 0.11g, 304.37g/mol, 0.35mmol) and palladium (II) acetate (1% eq, 0.02g, 224.51g/mol, 0.07mmol) in sequence, heating to reflux, stirring for reaction for 15h, cooling to room temperature, filtering, separating out toluene, extracting an aqueous phase with toluene, combining organic phases, washing with water, drying, concentrating under reduced pressure to obtain a crude product, purifying the crude product by column chromatography to obtain an organic compound (42.42) (31 g), yield 86.5%), MS (EI) 715.3(M + H)+。
And (3) testing a device:
application example 1
Putting the ITO glass substrate in distilled water, washing for 30min by 200W ultrasonic oscillation, washing with isopropanol, acetone and methanol in sequence after the washing is finished, drying and then sending to an evaporation machine.
A hole injection layer HAT-CN (10nm), a hole transport layer NPB (5nm), a light-emitting layer, namely, the organic compound (1) (15nm) prepared by the invention, an electron transport layer Alq3(5nm), and an electron injection layer LiQ (2nm) were sequentially deposited on an ITO glass substrate which had been prepared, and thereafter magnesium (Mg) and silver (Ag) were mixed at a ratio of 9:1 at a cathode and deposited at a thickness of 15nm to obtain a cathode.
Application examples 2 to 6
Basically the same as in application example 1, except that the organic compound (1) in application example 1 was replaced with the organic compounds (4), (15), (29), (34), and (42), respectively.
The device test results are shown in table 1 below:
table 1:
Figure BDA0002238925600000121
Figure BDA0002238925600000131
the device test result shows that the organic compound of the invention is used as the material of the luminescent layer, the luminous efficiency of the OLED device is higher, and the OLED device prepared by the organic compound of the invention has low driving voltage, thereby reducing the power consumption, and the service life of the OLED device is improved by low-voltage driving.
It is noted that, herein, relational terms such as first and second, and the like may be used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Also, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus. Without further limitation, an element defined by the phrase "comprising an … …" does not exclude the presence of other identical elements in a process, method, article, or apparatus that comprises the element.
The above examples are only intended to illustrate the technical solution of the present invention, but not to limit it; although the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; and such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions of the embodiments of the present invention.

Claims (9)

1. An organic compound based on a nitrogen-containing heterocycle, wherein the organic compound has the following structural formula:
Figure FDA0002238925590000011
wherein R is1、R2Each independently is hydrogen, deuterium, cyano, halogen atom, substituted or unsubstituted C1-C20 straight-chain alkyl or branched-chain alkyl, substituted or unsubstituted C6-C30 aromatic hydrocarbon group, substituted or unsubstituted C5-C30 heteroaromatic hydrocarbon group;
L1、L2each independently is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl;
X1、X2、X3、X4、X5、Y1、Y2、Y3、Y4、Y5each independently is C (R)3)、N；
The ring A and the ring B are the same in structure or mirror images of each other;
R3is any one of hydrogen, heavy hydrogen, cyano, halogen atoms, C1-C4 linear alkyl or branched alkyl, C6-C12 aromatic hydrocarbon;
m and n are each independently 1 or 2.
2. The nitrogen-containing heterocycle based organic compound of claim 1, wherein R is1、R2Each independently selected from cyano, phenyl, anthracenyl, naphthyl, phenanthryl, 9-dimethylfluorenyl, 9-spirobifluorenyl, oxyfluorenyl and thiofluorenyl.
3. The nitrogen-containing heterocycle based organic compound of claim 1, wherein L is1、L2Each independently is a group of the formula:
Figure FDA0002238925590000021
4. the nitrogen-containing heterocycle based organic compound of claim 1, wherein R is3Is any one of hydrogen, heavy hydrogen, fluorine atom, methyl and phenyl.
5. The nitrogen-containing heterocycle based organic compound of claim 1, wherein the organic compound is any one of compounds represented by the following structural formula:
Figure FDA0002238925590000022
Figure FDA0002238925590000031
6. the nitrogen-containing heterocycle based organic compound of claim 1, wherein the organic compound is prepared by the following method:
Figure FDA0002238925590000042
adding the raw material (I), the raw material (II) and sodium carbonate into a mixed solvent consisting of toluene and water, stirring and uniformly mixing, then sequentially adding tri (o-tolyl) phosphine and palladium (II) acetate, heating to reflux, stirring and reacting for 10-15h, cooling to room temperature after the reaction is finished, filtering, separating toluene, extracting a water phase with toluene, combining organic phases, washing with water, drying, concentrating under reduced pressure to obtain a crude product, and purifying the crude product by column chromatography to obtain the organic compound.
7. The nitrogen-heterocycle based organic compound of claim 6, wherein the mass ratio of the raw material (I), the raw material (II), sodium carbonate, tri (o-tolyl) phosphine, and palladium (II) acetate is 1:2-2.1:4: 5-10% to 1%.
8. Use of an organic compound based on a nitrogen-containing heterocycle according to any one of claims 1 to 5 for the preparation of an OLED device.
9. An OLED device, which is characterized by comprising an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode, wherein the light-emitting layer contains at least one organic compound based on a nitrogen-containing heterocycle according to any one of claims 1 to 5.
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Application publication date: 20200218